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Abstract

In the title compound, C38H32F2N4O4S, the ethyl chain of the ethoxy­carbonyl group displays rotational disorder with site occupancy factors ca 0.6 and 0.4. The S atom lies on a twofold rotation axis. There are both inter- and intra­molecular hydrogen bonds in the crystal structure. An intra­molecular N—HO hydrogen bond forms a six-membered ring, while an inter­molecular N—HF hydrogen bond results in a chain.

Acknowledgments

This project was supported by the National Science Found­ation of China (No. 20572057), the Natural Science Foundation of Shandong Province (Y2006B11) and the Doctoral Foundation of Qingdao University of Science and Technology.

supplementary crystallographic
information

Comment

Organic sulfides represent important building blocks in organic and medicinal
chemistry (Barton et al., 1979) due to their diverse biological and
pharmacological properties (Herradura et al., 2000). Because of their
synthetic and biological potential, considerable interest has been focused on
the synthesis of organic sulfides (Yin et al., 1997). In addition,
polysubstituted pyrroles are molecular frameworks having immense importance in
material science (Baumgarten et al., 1998). In order to develop new
biological activities, we synthesized the title compound, (I) (Fig.1), the
structure of which is reported here.

The title compound adopts a V conformation, which contains two parts which are
same to each other, and each part comprises three rings, two phenyl rings and
one pyrrole ring. In each part, the two phenyl rings are not conjugated with
the pyrrole ring, with the dihedral angle of 49.07° and 73.04°,
respectively.

All the bond lengths and angles (Table 1) in the title compound are within the
normal range. The bond lengths of C7—C8 (1.356 Å) and C9—C10 (1.380 Å)
in the pyrrole ring is obviously shorter than C—C (1.52 Å) but are close
to normal C?C (1.32 Å), it is indicated that they are both C?C. The bond
length of C7—C10 (1.454 Å) is between C—C and C?C.

X-ray analysis reveals that there exists both intermolecular hydrogen and
intromolecular hydrogen bonds in the crystal structure (Fig. 2). The
intromolecular N2—H2B···O1 hydrogen bond forms a six-membered ring, while
the intermolecular N2—H2A···F1 hydrogen bond makes the molecule extended in
line.

Experimental

A mixture of 2-(4-fluorophenyl)-2-oxo-N-phenylethanethioamide (3 mmol,
0.819 g), ethyl 2-cyanoacetate (3 mmol, 0.339 g), 10% NaOH solution (0.5 ml),
and 15 ml e thanol in a 25 ml flask was stirred for 3 h at room temperature
(monitored by TLC). The yellow solid was got by filtering. And then the solid
was added to a stirred solution of acetic acid (1 ml) in ethanol (15 ml) at
313 K under MW for 30 min. After cooling to room temperature, the solid
product was then got by filtering. The pure product was purified by
recrystallization from ethanol (m.p. 498 K).

Refinement

All H atoms were placed in calculated positions, with C—H distances in the
range 0.93 - 0.97 Å, and N—H = 0.90 Å and included in the final cycles
of refinement using a riding model, with Uiso(H) = 1.2 or
1.5Ueq(C,N). The ethyl chain of the ethoxycarbonyl group
displays rotational disorder. The site-occupation factors of the disordered
atoms C12, C13 and C12', C13' refined to 0.588 (14) and 0.412 (146),
respectively.

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.